Triethylamine → 3-[3-(3,3-Dimethylbutyl)-3-azabicyclo[3.1.0]hexane-6-carboxamido]methyl-5-isobutyl-1-phenyl-1H-pyrazole

Participants

Reaction Steps

The 6-((5-isobutyl-1-phenyl-1H-pyrazole-3-yl)methylcarbamoyl)-3-azabicyclo[3.1.0]hexane hydrochloride (93.5 mg, 0.249 mmol) prepared in Example 11 and a molecular sieve were dried in vacuum and dissolved in 2 mL of methylene chloride. Then, triethylamine (35 μL, 0.249 mmol) was added dropwise at 0° C. After adding 3,3-dimethylbutyraldehyde (31 μL, 0.249 mmol) dropwise, the mixture was stirred at room temperature for 1 hour. After adding sodium triacetoxyborohydride (159 mg, 0.748 mmol), the mixture was stirred for 2 hours and 30 minutes. The completion of the reaction was confirmed by TLC (hexane:ethyl acetate=1:2). After the reaction was completed, the reaction mixture was diluted with methylene chloride and extracted several times with saturated sodium bicarbonate. The organic layer was dried with anhydrous magnesium sulfate, filtered, concentrated under reduced pressure and separated by column chromatography (CH2Cl2:MeOH=15:1) to obtain 67.3 mg (63.9%) of the target compound.

Provenance & Evidence